I've been in the insurance business for about 25 years now, and have owned my own shop for 10 years. If I could make some suggestions - and I don't mean this with any sarcasm.
Find yourself an agent or broker that you are comfortable with. Basically, interview them. Most agents should have multiple companies that they represent, including some of those "direct" guys like Allstate, Progressive, etc. Now instead of you (and I mean whoever, not "you") contacting Allstate, State Farm, Progressive, GEICO, etc... you have someone else doing the legwork for you.
Contrary to popular belief, it does not necessarily cost you more to work with an agent or broker. Yes, they work on a commission to get paid. But rates are rates. Each insurance company is filed for set rates in a given state. So if Company A says we get $100 to insure a car worth $10,000 with $100,000 in liability (these are just made up numbers), they can't, by law, randomly say we want $500 to insure that car so we can pay the insurance broker their commission.
The idea of having an agent/broker is to have someone that actually understands insurance in order to help you. Look, when we need to re-wire our house, we call an electrician. If our toilet is backed up, we call a plumber. If we break a finger, we go to a doctor. For guys like me who can't turn a wrench, I pay a mechanic. Again I don't mean any disrespect with this, but I think too many people have no idea what they are doing with insurance, yet so many of them feel they can handle their coverage selections by themselves. Aside from your car potentially being an asset, consider the fact that we live in a highly litigious society. One wrong click of a button on the screen, and you could really be selecting insurance that just isn't right - either for your car, or for your financial security if something horrible were to happen (i.e. an accident involving injuries).
Insurance policies are lengthy and tedious. Even after 25 years in the business, trust me, if legal action were to ensue in the event of a loss, attorney's can dig through that policy and spin it in ways that you'd never think.
Which leads to the next point: Again, in the event of an accident or loss, by having an agent, you now actually have someone that should be on your side. A claims person to contact the company. Most of them should have the bat-line right to the company. You? You're stuck dialing an 800 number and entering a boatload of info to the computerized voice only to have a person eventually pick up so you can tell them your info all over again. Someone to help you sort through all the verbiage and potential legalities of the policy could be beneficial.
Last thing: despite my involvement in the insurance business, I still use an agent for ALL my personal insurance. For exactly the reasons I mentioned above. I want somebody that's on my side, and in the event that something is eff'd up on my policy, I have someone else to fall back to. I'd much rather have somebody (and that could be the customer service rep, the claims manager, and maybe even an owner if your lucky) in the ring with me if I have to go an battle the 800# insurance company gorilla.
Man, I hate insurance.
